Tolylboronic acid → Methyl 2-(4-phenyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate

HRID 1399733Notes

Reaction equation

HRID 1399733 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([C:8]1[C:9](Cl)=[N:10][C:11]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[N:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][CH2:6][CH3:7].B(O)(O)[C:29]1[CH:30]=[CH:31][C:32](C)=[CH:33][CH:34]=1.[CH:38](N(CC)C(C)C)(C)C>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:29]1([C:9]2[C:8]([CH:4]([CH2:5][CH2:6][CH3:7])[C:3]([O:2][CH3:1])=[O:27])=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([CH3:38])=[CH:16][CH:15]=3)[N:12]=[C:11]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[N:10]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 79799Tolylboronic acidHCID 81531DiisopropylethylamineHCID 86665655Methyl 2-(4-chloro-6-phenyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate

Product 1

HCID 66955993Methyl 2-(4-phenyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoateYield 45%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

methyl-2-(4-chloro-6-phenyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.031 g; 0.228 mmol), p-tolylboronic acid (0.031 g; 0.228 mmol), tetrakis(triphenylphosphine) palladium(0) (0.013 g; 0.011 mmol) were placed in a 5 mL reaction tube and dissolved in a mixture of degassed DME (0.75 mL) and water (0.25 mL). N,N-Diisopropylethylamine (0.060 mL; 0.344 mmol) was added, the tube was sealed and irradiated in a microwave oven at 130° C. for 30 min. The reaction mixture was partitioned between a solution of hydrochloric acid 1N and ethyl acetate. The phases were separated and the organic phase was washed with a 1N sodium bicarbonate solution and a saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (0-10%) in heptane to give 0.018 g (45%) of the title compound.

Workup

  1. customthe tube was sealed
  2. customirradiated in a microwave oven at 130° C. for 30 min
  3. customThe reaction mixture was partitioned between a solution of hydrochloric acid 1N and ethyl acetate
  4. customThe phases were separated
  5. washthe organic phase was washed with a 1N sodium bicarbonate solution
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (0-10%) in heptane

Sources & evidence

ORD record
ord-749c04f88a374c6aa476b524951cee64
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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